Ethyl benzoylacetate → N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]-beta-oxobenzenepropanamide

HRID 1886351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886351
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[O:20]=[C:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:22][C:23](OCC)=[O:24]>C1C=CC=CC=1>[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:23](=[O:24])[CH2:22][C:21](=[O:20])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

4

Edukt 2

HCID 7170Ethyl benzoylacetateHCID 145184254-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrobenzenamine

Produkt 1

HCID 19875839N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]-beta-oxobenzenepropanamideAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 10 parts of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrobenzenamine, 20 parts of ethyl β-oxobenzenepropanoate and 174 parts of benzene was stirred for 36 hours at reflux temperature. After cooling, the reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 7 parts (44.8%) of N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]-β-oxobenzenepropanamide; mp. 106° C. (interm. 96).

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f5f335e54cb644dc9de0294372d97bc1
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05151421

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